Urban transit planning is going through a transition to greater private investment in many parts of the world and is now on the agenda in Australia. After showing examples of private investment in transit globally, the paper focuses on historical case studies of private rail investment in Western Australia. These case studies mirror the historical experience in rapidly growing railway cities in Europe, North America, and Asia (particularly Japan), and also the land grant railways that facilitated settlement in North America. The Western Australian experience is noteworthy for the small but rapidly growing populations of the settlements involved, suggesting that growth, rather than size, is the key to successfully raising funding for railways through land development. The paper shows through the history of transport, with particular reference to Perth, that the practice of private infrastructure provision can provide lessons for how to enable this again. It suggests that new partnerships with private transport investment as set out in the Federal Government City Deal process, should create many more opportunities to improve the future of cities through once again integrating transit, land development, and private finance.